1965
DOI: 10.1021/jf60142a010
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Radiolabeled Insecticides, Synthesis of Rotenon-6a-C14 on a Semimicro Scale

Abstract: Reaction of 2 mmoles of methyl bromoacetate-1 -C14 with 3 mmoles of derritol produced 6a,12a-dehydrorotenone-6a-C14 in approximately 50% yield. Sodium boron hydride reduction gave the 12-hydroxy-6a-C14 intermediate and subsequent Oppenauer oxidation produced rotenone-6a-C14. Yields for conversion of nonradioactive 6a,12a-dehydrorotenone to rotenone were 17 to 25% but, with radioactive material of 2.36 me. per mmole, the yield was only 7.5%. Other oxidation procedures for the reduction product of 6a,1 2a-dehydr… Show more

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Cited by 11 publications
(5 citation statements)
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“…Natural rotenone (Aldrich Chemical Co., Milwaukee, Wis.) was recrystallized from methanol [mp 162-3"C, reported as 162-3°C by Nishizawa and Casida (1965), and 167-8°C by Crombie (1963); [cu]*~D -226" in benzene, reported as [OI]~OD -228" in benzene by Crombie (1963)l. Natural rotenone (Aldrich Chemical Co., Milwaukee, Wis.) was recrystallized from methanol [mp 162-3"C, reported as 162-3°C by Nishizawa and Casida (1965), and 167-8°C by Crombie (1963); [cu]*~D -226" in benzene, reported as [OI]~OD -228" in benzene by Crombie (1963)l.…”
Section: Materials a N D Analytical Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…Natural rotenone (Aldrich Chemical Co., Milwaukee, Wis.) was recrystallized from methanol [mp 162-3"C, reported as 162-3°C by Nishizawa and Casida (1965), and 167-8°C by Crombie (1963); [cu]*~D -226" in benzene, reported as [OI]~OD -228" in benzene by Crombie (1963)l. Natural rotenone (Aldrich Chemical Co., Milwaukee, Wis.) was recrystallized from methanol [mp 162-3"C, reported as 162-3°C by Nishizawa and Casida (1965), and 167-8°C by Crombie (1963); [cu]*~D -226" in benzene, reported as [OI]~OD -228" in benzene by Crombie (1963)l.…”
Section: Materials a N D Analytical Methodsmentioning
confidence: 99%
“…Chemicals. Natural rotenone (Aldrich Chemical Co., Milwaukee, Wis.) was recrystallized from methanol [mp 162-3°C, reported as 162-3°C by Nishizawa and Casida (1965), and 167-8°C by Crombie (1963); [a]25D -226°in benzene, reported as [ ]20 -228°in benzene by Crombie (1963)].…”
Section: Materials and Analytical Methodsmentioning
confidence: 99%
“…The C14-labeled pesticide chemicals studied were prepared in this laboratory, in which case the labeled position has been reported (Krishna et al, 1962; Kuwatsuka and Casida, 1965;Nishizawa and Casida, 1965;Yamamoto and Casida, 1968), or they were obtained as follows: aldrin-C14, dieldrin-C14, endrin-C14, and 3,4,5-trimethylphenyl methylcarbamate carbonyl-C14 (SD-8530) (Shell Development Co., Modesto, Calif.); 2-dimethylamino-4,5-dimethyl-6-pyrimidyl dimethylcarbamate carbonyl-C14 (pirimicarb) (Alan Calderbank, Division of Entomology, University of California, Berkeley, Calif. 94720 Plant Protection Ltd., Jealott's Hill, England); Sumithion-O-methyl-C14 (Yoshihiko Nishizawa, Sumitomo Chemical Co., Osaka, Japan); Imidan-carbonyl-C14 and Dyfonatering-C14 (Julius Menn, Stauffer Chemical Co., Mountain View, Calif.); malathion-l,2-succinyl-C14 and DDT-ring-C14 (World Health Organization, Geneva, Switzerland); diazinon-pyrimidyl-2-C14 and isolan-carbonyl-C14 (Geigy Chemical Co., Ardsley, N.Y.); 2,4-D-a-C'4 (New England Nuclear Corp., Boston, Mass. ); Dessin-ring-C14 (Union Carbide Chemicals Co., South Charleston, W. Va.); and 2-jec-butyl-4,6-dinitrophenol-ring-C14 (DNBP) (obtained by hydrolysis of Dessin-ring-C14 and supplied by Suresh Bandal, University of Calif., Berkeley).…”
Section: Methodsmentioning
confidence: 99%
“…Recognition of a specific binding site for an insecticide in complex I was first achieved with [ 14 C] 1a (2.4 mCi mmol −1 )32 and bovine heart electron transport particles (ETP) (Fig 5). 33 A centrifugation assay was used with bovine serum albumin (BSA) washes of the ETP to minimize non‐specific binding.…”
Section: Insecticide Binding Sitementioning
confidence: 99%